How do you become an enterprise account executive? Do you have to have Saas experience? Or could you have been in sales in a different area? I worked for a real estate brokerage in NY and our team used to do over 250 million in sales a year. I’d average about 75 million. Would that count for anything?

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How would you position the relevance of real estate sales experience to enterprise sales? Are you selling to a similar buyer, or are the solutions addressing similar business needs? Enterprise tech deals are generally done because the ROI from doing the deal is compelling (eg, risk of inaction, improved productivity, long term cost savings, long term incremental revenue gains, etc). Typically, the starting point is to land a role where you will learn about how to position the enterprise tech offering to address customer business problems and win against competitors. This might be a consulting role, a sales development role, etc.

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Why would you leave a role so lucrative?

I’ve been in real estate for 15 years. I’m just pretty burnt out from it and want to try something else for a change.

In what industry vertical do you have dozens (preferably hundreds) of contacts who trust you that'll take a meeting with you if you change jobs?

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